Conformationally rigid analogs of aldose reductase inhibitor, tolrestat. Novel syntheses of naphthalene-fused .gamma.-, .delta.-, and .epsilon.-lactams

Trifluoromethylation of aryl and heteroaryl halides

“…99 As suggested by Yagupolskii, the trifluoromethylcopper (I) species was first generated in situ by pre-heating a solution of (CF 3 ) 2 Hg (0.6 equiv) and activated copper powder (2.4 equiv) in DMAC at 145 C after which the iodide was added dropwise and stirred at 150e155 C for 1 h. The desired product was isolated in nearly quantitative yield. The authors reported that the corresponding bromide precursor completely failed to give the desired product under the same reaction conditions, indicating that aryl bromides are not attractive substrates for this trifluoromethylation method.…”

Synthesis of naphtho[1,2‐b]‐, naphtho[2,1‐b]‐, and naphtho[2,3‐b]azepinones via proton‐induced cyclization of N‐1(2)‐naphthyl styrylacetamides

“…In the recent years, the scope of fused 1 Н ‐azepines under study has been significantly extended by inclusion of their naphtho[ b ]‐fused derivatives; some of which act as potent growth hormone secretagogues, γ‐secretase modulators, aldose reductase inhibitors, tranquilizers, anti‐human immunodeficiency virus (HIV) and antiparasitic drugs, and dopamine receptor agonists …”

Synthesis of Fluorescence‐Labelled Glycosidic Prodrugs Based on the Cytotoxic Antibiotic Duocarmycin

“…Nitrile reduction in (1S)-27a and (1S,10R)-27b in accordance with the method of Wrobel et al [11] with PtO 2 ·H 2 O under H 2 afforded the corresponding primary amines 28a and 28b (Scheme 10), and these were deprotected under basic conditions with NaOMe in MeOH to give the desired aminomethyl-substituted prodrugs (1S)-3a and (1S,10R)-3b.…”